ES2206534T3 - Derivados de sulfonil-o sulfinil-benzoil-guanidina. - Google Patents

Info

Publication number

ES2206534T3

ES2206534T3 ES96112498T ES96112498T ES2206534T3 ES 2206534 T3 ES2206534 T3 ES 2206534T3 ES 96112498 T ES96112498 T ES 96112498T ES 96112498 T ES96112498 T ES 96112498T ES 2206534 T3 ES2206534 T3 ES 2206534T3

Authority

ES

Spain

Prior art keywords

diaminomethylene

benzamide

methyl

methylsulfonyl

ethyl

Prior art date

1995-08-11

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

Links

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• 150000003839 salts Chemical class 0.000 claims abstract description 19
• 150000001875 compounds Chemical class 0.000 claims description 57
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 40
• 239000002253 acid Substances 0.000 claims description 26
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 20
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 16
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 229910052740 iodine Inorganic materials 0.000 claims description 13
• 239000002904 solvent Substances 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 238000000034 method Methods 0.000 claims description 10
• AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 201000010099 disease Diseases 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 239000003054 catalyst Substances 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 239000007800 oxidant agent Substances 0.000 claims description 5
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• 239000007788 liquid Substances 0.000 claims description 4
• 208000010125 myocardial infarction Diseases 0.000 claims description 4
• GROMEQPXDKRRIE-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4,5-bis(methylsulfonyl)benzamide Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N GROMEQPXDKRRIE-UHFFFAOYSA-N 0.000 claims description 4
• RSKNQTWLPWOKCV-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O RSKNQTWLPWOKCV-UHFFFAOYSA-N 0.000 claims description 3
• 206010002383 Angina Pectoris Diseases 0.000 claims description 3
• 102000003669 Antiporters Human genes 0.000 claims description 3
• 108090000084 Antiporters Proteins 0.000 claims description 3
• 230000006793 arrhythmia Effects 0.000 claims description 3
• 206010003119 arrhythmia Diseases 0.000 claims description 3
• SSSFMJQBOLXYLC-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4,5-bis(methylsulfonyl)benzamide Chemical compound CCC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N SSSFMJQBOLXYLC-UHFFFAOYSA-N 0.000 claims description 3
• 239000012038 nucleophile Substances 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 230000003449 preventive effect Effects 0.000 claims description 3
• UJURHIFLDARYMY-UHFFFAOYSA-N 4-cyclohexylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C2CCCCC2)=C1S(C)(=O)=O UJURHIFLDARYMY-UHFFFAOYSA-N 0.000 claims description 2
• BJWRCFVWJBOFDD-UHFFFAOYSA-N 4-tert-butylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(S(=O)(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N BJWRCFVWJBOFDD-UHFFFAOYSA-N 0.000 claims description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
• 239000003638 chemical reducing agent Substances 0.000 claims description 2
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
• 239000002552 dosage form Substances 0.000 claims description 2
• DCDPUQNQPMGSTK-UHFFFAOYSA-N n-(diaminomethylidene)-4-sulfinylcyclohexa-1,5-diene-1-carboxamide Chemical compound NC(N)=NC(=O)C1=CCC(=S=O)C=C1 DCDPUQNQPMGSTK-UHFFFAOYSA-N 0.000 claims description 2
• 229910052757 nitrogen Inorganic materials 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• XRZBZLIYXKXYFJ-UHFFFAOYSA-N 4-cyclopentylsulfonyl-n-(diaminomethylidene)-2-ethylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C2CCCC2)=C1 XRZBZLIYXKXYFJ-UHFFFAOYSA-N 0.000 claims 1
• MDDZBMOWENBNCP-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-methyl-4-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(C)(=O)=O)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 MDDZBMOWENBNCP-UHFFFAOYSA-N 0.000 claims 1
• 230000005764 inhibitory process Effects 0.000 claims 1
• 239000012439 solid excipient Substances 0.000 claims 1
• 239000012453 solvate Substances 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 2
• -1 isopentyl (3-methylbutyl) Chemical group 0.000 description 175
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 133
• 238000006243 chemical reaction Methods 0.000 description 45
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 125000006239 protecting group Chemical group 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 239000011734 sodium Substances 0.000 description 8
• 239000000203 mixture Substances 0.000 description 7
• 230000003647 oxidation Effects 0.000 description 7
• 238000007254 oxidation reaction Methods 0.000 description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 125000002252 acyl group Chemical group 0.000 description 6
• 125000003118 aryl group Chemical group 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 238000007327 hydrogenolysis reaction Methods 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• 230000009466 transformation Effects 0.000 description 5
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 4
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• 229960000583 acetic acid Drugs 0.000 description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• 150000001408 amides Chemical class 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 210000000056 organ Anatomy 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 4
• 230000001012 protector Effects 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
• 206010021143 Hypoxia Diseases 0.000 description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 150000001263 acyl chlorides Chemical class 0.000 description 3
• 230000003288 anthiarrhythmic effect Effects 0.000 description 3
• 235000010233 benzoic acid Nutrition 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 210000004027 cell Anatomy 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 150000002148 esters Chemical class 0.000 description 3
• 125000000623 heterocyclic group Chemical group 0.000 description 3
• 239000001257 hydrogen Substances 0.000 description 3
• 239000012442 inert solvent Substances 0.000 description 3
• 239000000543 intermediate Substances 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 239000000454 talc Substances 0.000 description 3
• 235000012222 talc Nutrition 0.000 description 3
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• 230000001225 therapeutic effect Effects 0.000 description 3
• 238000002560 therapeutic procedure Methods 0.000 description 3
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
• 230000000699 topical effect Effects 0.000 description 3
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
• YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
• XNFHCESYDYHGSU-UHFFFAOYSA-N 4-cyclopentylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C2CCCC2)=C1S(C)(=O)=O XNFHCESYDYHGSU-UHFFFAOYSA-N 0.000 description 2
• HMCYHOSMWJTVNB-UHFFFAOYSA-N 4-cyclopentylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C2CCCC2)=C1S(C)(=O)=O HMCYHOSMWJTVNB-UHFFFAOYSA-N 0.000 description 2
• AAYFCBWYUQEYIK-UHFFFAOYSA-N 4-cyclopropylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C2CC2)=C1S(C)(=O)=O AAYFCBWYUQEYIK-UHFFFAOYSA-N 0.000 description 2
• KIAHGXHIYYBNTF-UHFFFAOYSA-N 4-cyclopropylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C2CC2)=C1S(C)(=O)=O KIAHGXHIYYBNTF-UHFFFAOYSA-N 0.000 description 2
• 206010003210 Arteriosclerosis Diseases 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• 241000282472 Canis lupus familiaris Species 0.000 description 2
• 241000282693 Cercopithecidae Species 0.000 description 2
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• 241000699670 Mus sp. Species 0.000 description 2
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• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
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• 239000003416 antiarrhythmic agent Substances 0.000 description 2
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• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
• 229940054066 benzamide antipsychotics Drugs 0.000 description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 239000003153 chemical reaction reagent Substances 0.000 description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 239000012154 double-distilled water Substances 0.000 description 2
• 239000008298 dragée Substances 0.000 description 2
• 150000002170 ethers Chemical class 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
• 229940093915 gynecological organic acid Drugs 0.000 description 2
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• 150000002430 hydrocarbons Chemical class 0.000 description 2
• 230000001146 hypoxic effect Effects 0.000 description 2
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• 208000028867 ischemia Diseases 0.000 description 2
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• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
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